Ciproheptadin

Ciproheptadin
IUPAC ime
	4-(5H-dibenzo [a,d]ciklohepten-5-iliden)-1-metilpiperidin hidrohlorid
Klinički podaci
Prodajno ime	Periaktin
Drugs.com	Monografija
MedlinePlus	a682541
Kategorija trudnoće	US: B (Bez rizika u ispitivanjima na životinjama) ; ;
Način primene	Oralno
Pravni status
Pravni status	UK: Samo u apoteci ;
Farmakokinetički podaci
Vezivanje proteina	96 do 99%
Metabolizam	Hepatički i renalno
Poluvreme eliminacije	8,6 sata
Izlučivanje	Fekalno i renalno
Identifikatori
CAS broj	129-03-3 969-33-5 (hidrohlorid)
ATC kod	R06AX02 (WHO)
PubChem	CID 2913
IUPHAR/BPS	277
DrugBank	DB00434
ChemSpider	2810
UNII	2YHB6175DO
KEGG	D07765
ChEBI	CHEBI:4046
ChEMBL	CHEMBL516
Hemijski podaci
Formula	C21H21N
Molarna masa	287,398 g/mol
	SMILES c43\C(=C1/CCN(C)CC1)c2ccccc2\C=C/c3cccc4; ;
	InChI InChI=1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3 ; Key:JJCFRYNCJDLXIK-UHFFFAOYSA-N ;

Ciproheptadin (Periaktin) je prva generacija antihistamina sa dodatnim antiholinergičnim, antiserotinergičnim, i lokalno anestetičkim svojstvima.^[2]^[3]

Farmakologija

Ciproheptadin deluje kao antagonist (ili inverzni agonist u zavisnosti od aktivnog mesta) na sledećim receptorima:

H₁ (~0,05 nM)^[4] > 5-HT_2A (~2 nM)^[5] ≈ 5-HT_2B (~1,5 nM)^[6] ≈ 5-HT_2C (~2 nM)^[6] > mACh (M₁-M₅; ~7-12 nM)^[7] ≈ D₃ (~8 nM)^[8]

On ima slab, i verovatno zanemarljiv, afinitet za sledeća mesta vezivanja (K_i):

5-HT_1A (~60-100 nM)^[5]^[8] ≈ α₁-adrenergički (?? nM)^[9] ≈ α₂-adrenergički (?? nM)^[9] > 5-HT₆ (~135-150 nM)^[10]^[11] ≈ 5-HT₇ (~125 nM)^[11] ≈ D₁ (~115 nM)^[8] ≈ D₂ (~115 nM)^[8] > 5-HT_3</sub> (~250 nM)^[8]^[12] ≈ NET (~300 nM)^[13]

Pored toga, ciproheptadin poseduje osobine blokatora kalcijumskog kanala^[14] i lokalnog anestetika.^[15]

Reference

^ Gunja N, Collins M, Graudins A (2004). „A comparison of the pharmacokinetics of oral and sublingual cyproheptadine”. Journal of Toxicology. Clinical Toxicology. 42 (1): 79—83. PMID 15083941.
^ Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803.
^ Pdr Staff (2009). PDR: Physicians Desk Reference 2010 (Physicians' Desk Reference (Pdr)). Rozelle, N.S.W: Thomson Reuters. ISBN 1-56363-748-0.
^ Moguilevsky, N.; F, Varsalona; Noyer, M.; et al. (1994). „Stable expression of human H1-histamine-receptor cDNA in Chinese hamster ovary cells. Pharmacological characterisation of the protein, tissue distribution of messenger RNA and chromosomal localisation of the gene”. European Journal of Biochemistry / FEBS. 224 (2): 489—95. PMID 7925364. doi:10.1111/j.1432-1033.1994.00489.x.
^ ^а ^б Peroutka, S. J. (1988). „Antimigraine drug interactions with serotonin receptor subtypes in human brain”. Annals of Neurology. 23 (5): 500—4. PMID 2898916. doi:10.1002/ana.410230512.
^ ^а ^б Bonhaus, D. W.; Weinhardt, K. K.; Taylor, M.; et al. (1997). „RS-102221: a novel high affinity and selective, 5-HT2C receptor antagonist”. Neuropharmacology. 36 (4–5): 621—9. PMID 9225287. doi:10.1016/S0028-3908(97)00049-X.
^ Stanton T, Bolden-Watson C, Cusack B, Richelson E (1993). „Antagonism of the five cloned human muscarinic cholinergic receptors expressed in CHO-K1 cells by antidepressants and antihistaminics”. Biochemical Pharmacology. 45 (11): 2352—4. PMID 8100134. doi:10.1016/0006-2952(93)90211-E.
^ ^а ^б ^в ^г ^д Toll, L.; Berzetei-Gurske IP; Polgar, W. E.; et al. (1998). „Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications”. NIDA Research Monograph. 178: 440—66. PMID 9686407.
^ ^а ^б Dukhovich, F. S. (15. 8. 2005). Pharmacological aspects of molecular recognition. Nova Publishers. стр. 117. ISBN 978-1-59454-676-1. Приступљено 27. 11. 2011.
^ Kohen, R.; Metcalf, M. A.; Khan, N.; et al. (1996). „Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor”. Journal of Neurochemistry. 66 (1): 47—56. PMID 8522988. doi:10.1046/j.1471-4159.1996.66010047.x.
^ ^а ^б Bard JA, Zgombick J, Adham N, Vaysse P, Branchek TA, Weinshank RL (1993). „Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase”. The Journal of Biological Chemistry. 268 (31): 23422—6. PMID 8226867.
^ Hoyer D, Neijt HC (1988). „Identification of serotonin 5-HT3 recognition sites in membranes of N1E-115 neuroblastoma cells by radioligand binding”. Molecular Pharmacology. 33 (3): 303—9. PMID 3352595.
^ Runyon SP, Savage JE, Taroua M, Roth BL, Glennon RA, Westkaemper RB (2001). „Influence of chain length and N-alkylation on the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene”. Bioorganic & Medicinal Chemistry Letters. 11 (5): 655—8. PMID 11266163. doi:10.1016/S0960-894X(01)00023-3.
^ Lowe DA, Matthews EK, Richardson BP (1981). „The calcium antagonistic effects of cyproheptadine on contraction, membrane electrical events and calcium influx in the guinea-pig taenia coli”. British Journal of Pharmacology. 74 (3): 651—63. PMC 2071752 . PMID 6271323.
^ F, Riccioppo Neto (1979). „The local anesthetic effect of cyproheptadine on mammalian nerve fibres”. European Journal of Pharmacology. 54 (3): 203—7. PMID 428422. doi:10.1016/0014-2999(79)90078-5.

Literatura

Dukhovich, F. S. (2005). Pharmacological aspects of molecular recognition. Nova Publishers. стр. 117. ISBN 978-1-59454-676-1. Приступљено 27. 11. 2011.

Spoljašnje veze

Molimo Vas, obratite pažnju na važno upozorenje
u vezi sa temama iz oblasti medicine (zdravlja).

[pmid15083941-1] Gunja N, Collins M, Graudins A (2004). „A comparison of the pharmacokinetics of oral and sublingual cyproheptadine”. Journal of Toxicology. Clinical Toxicology. 42 (1): 79—83. PMID 15083941.

[Goodman_Gilman-2] Hardman JG, Limbird LE, Gilman AG (2001). Goodman & Gilman's The Pharmacological Basis of Therapeutics (10. изд.). New York: McGraw-Hill. ISBN 0071354697. doi:10.1036/0071422803.

[PDR-3] Pdr Staff (2009). PDR: Physicians Desk Reference 2010 (Physicians' Desk Reference (Pdr)). Rozelle, N.S.W: Thomson Reuters. ISBN 1-56363-748-0.

[pmid7925364-4] Moguilevsky, N.; F, Varsalona; Noyer, M.; et al. (1994). „Stable expression of human H1-histamine-receptor cDNA in Chinese hamster ovary cells. Pharmacological characterisation of the protein, tissue distribution of messenger RNA and chromosomal localisation of the gene”. European Journal of Biochemistry / FEBS. 224 (2): 489—95. PMID 7925364. doi:10.1111/j.1432-1033.1994.00489.x.

[pmid2898916-5] а ^б Peroutka, S. J. (1988). „Antimigraine drug interactions with serotonin receptor subtypes in human brain”. Annals of Neurology. 23 (5): 500—4. PMID 2898916. doi:10.1002/ana.410230512.

[pmid9225287-6] а ^б Bonhaus, D. W.; Weinhardt, K. K.; Taylor, M.; et al. (1997). „RS-102221: a novel high affinity and selective, 5-HT2C receptor antagonist”. Neuropharmacology. 36 (4–5): 621—9. PMID 9225287. doi:10.1016/S0028-3908(97)00049-X.

[pmid8100134-7] Stanton T, Bolden-Watson C, Cusack B, Richelson E (1993). „Antagonism of the five cloned human muscarinic cholinergic receptors expressed in CHO-K1 cells by antidepressants and antihistaminics”. Biochemical Pharmacology. 45 (11): 2352—4. PMID 8100134. doi:10.1016/0006-2952(93)90211-E.

[pmid9686407-8] а ^б ^в ^г ^д Toll, L.; Berzetei-Gurske IP; Polgar, W. E.; et al. (1998). „Standard binding and functional assays related to medications development division testing for potential cocaine and opiate narcotic treatment medications”. NIDA Research Monograph. 178: 440—66. PMID 9686407.

[Dukhovich2005-9] а ^б Dukhovich, F. S. (15. 8. 2005). Pharmacological aspects of molecular recognition. Nova Publishers. стр. 117. ISBN 978-1-59454-676-1. Приступљено 27. 11. 2011.

[pmid8522988-10] Kohen, R.; Metcalf, M. A.; Khan, N.; et al. (1996). „Cloning, characterization, and chromosomal localization of a human 5-HT6 serotonin receptor”. Journal of Neurochemistry. 66 (1): 47—56. PMID 8522988. doi:10.1046/j.1471-4159.1996.66010047.x.

[pmid8226867-11] а ^б Bard JA, Zgombick J, Adham N, Vaysse P, Branchek TA, Weinshank RL (1993). „Cloning of a novel human serotonin receptor (5-HT7) positively linked to adenylate cyclase”. The Journal of Biological Chemistry. 268 (31): 23422—6. PMID 8226867.

[pmid3352595-12] Hoyer D, Neijt HC (1988). „Identification of serotonin 5-HT3 recognition sites in membranes of N1E-115 neuroblastoma cells by radioligand binding”. Molecular Pharmacology. 33 (3): 303—9. PMID 3352595.

[pmid11266163-13] Runyon SP, Savage JE, Taroua M, Roth BL, Glennon RA, Westkaemper RB (2001). „Influence of chain length and N-alkylation on the selective serotonin receptor ligand 9-(aminomethyl)-9,10-dihydroanthracene”. Bioorganic & Medicinal Chemistry Letters. 11 (5): 655—8. PMID 11266163. doi:10.1016/S0960-894X(01)00023-3.

[pmid6271323-14] Lowe DA, Matthews EK, Richardson BP (1981). „The calcium antagonistic effects of cyproheptadine on contraction, membrane electrical events and calcium influx in the guinea-pig taenia coli”. British Journal of Pharmacology. 74 (3): 651—63. PMC 2071752 . PMID 6271323.

[pmid428422-15] F, Riccioppo Neto (1979). „The local anesthetic effect of cyproheptadine on mammalian nerve fibres”. European Journal of Pharmacology. 54 (3): 203—7. PMID 428422. doi:10.1016/0014-2999(79)90078-5.

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